Before I began working with Jaime Richards, one of the matchmakers in this week's cover story, I had to dig deep. Really deep. It's common practice for date coaches and matchmakers to ask their clients for letters of recommendation, but they're not the kind you're thinking of. In preparation for our first meeting, I was tasked with asking a minimum of six friends and family members to write Richards letters explaining why they think I'm single.

The phone calls behind this were awkward ("Hey, co-worker, can you e-mail this woman and comment on my love life?"), but I wanted to go through the entire process that Richards's regular clients do. The written responses were accompanied by my own answers to a survey in which I summed up my past relationship history. The result is a personal assessment accompanied by a generous amount of fodder to begin creating an online dating profile.

From here, Richards approaches each of her clients differently. With some, she personally compiles all of the information she has collected from friends and writes the dating bio herself. With others, she sits next to them and advises them as they do it on their own. Before we met, she created an outline of what she did and didn't want me to highlight about myself, and the two categories were fairly equal.

Jaime Richards.

Jim J. Narcy

"The goal is to create a marketing profile that targets the right person," Richards says. "Online, everyone's single greatest fear is rejection, so I work to make my clients seem friendly and approachable while still a little mysterious. The worst things online are negativity and dishonesty."

On the list of things to keep were outgoing activities and cultural interests, while anything that can be misconstrued as an overachievement should be saved for later, she says. This means that my interest in road trips made the cut, but my master's degree did not. And the amount of time I spent covering Occupy Denver was definitively off limits.

When creating an online dating profile, Richards advises her clients to begin their bios with a greeting of sorts and end it with a statement that the photos above it are recent. She is a staunch supporter of winking, the online equivalent of flirting, and she encourages a generous amount of outgoing messages and winks on a daily basis. (Match.com once temporarily blocked her IP address after she winked at too many people for a client.)

She devotes her entire focus to her clients, whom she spends a great deal of time getting to know. When I met with her to create my online image, she invited me into her home and created a Brit-pop-friendly Pandora station based on the knowledge my friends shared with her. Once her clients' profiles are finished, the idea is to narrow down quantity after first broadcasting to quantity. And while large numbers are a boon when it comes to the number of people you greet, they are bad when it comes to how long that greeting lasts.

"Don't let them just pen-pal you to death," Richards says. "If they e-mail you more than three times, they're scared to ask you out, and you have to get things going faster than that."

Richards emphasizes dropping your "type" when it comes to online dating. While the two separate men from Hoover, Alabama who were 28 years my senior might not be options, she says, clients should enter the process with the idea that anyone can be. This idea is echoed in the mildly creepy introductory e-mail with which Match.com greets new daters: "Your new love life awaits."

The next step -- which Richards and I walked through in preparation for Monday's blog post -- is the first date. According to Richards's strategy, the entire goal of the first date should be to guarantee a second one.

In the meantime, here are some tips from Richard on preparing for a first date:1. Women, change out of your work clothes, even if you have to bring a change of clothes with you.

2. If possible, go home and do what you need to do to relax, unwind, and come out of work mode before heading out.

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3. Whatever you do, do not go out with a negative attitude toward the opposite sex. It will come through no matter what!

4. Make sure you're on time! Do not cancel on someone last-minute unless it's absolutely unavoidable (like the stomach flu, or a car accident). Doing so says "I'm more important than you are." No one wants to feel that way.

5. Turn off your cell phone when you arrive and don't set it face up on the table!